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Synthesis 2024; 56(24): 3870-3878
DOI: 10.1055/a-2435-5589
DOI: 10.1055/a-2435-5589
paper
Pd/Mengphos-Catalyzed High-Order [4+4] Cycloaddition for Efficient Synthesis of Oxazocines
We are grateful to the National Natural Science Foundation of China (21702189), the Science and Technology Research and Development Plan Joint Fund (cultivation of superior disciplines project 222301420042), Hanjiang Normal University (2024B09), and Zhengzhou University of China for financial support of this research.
Abstract
The development of new catalytic systems that enable regio- and chemoselective construction of diversely functionalized oxazocines is an important topic in organic synthesis and pharmacochemistry. Herein, a novel Pd/Mengphos complex was designed and applied in a palladium-catalyzed high-order [4+4] cycloaddition of 2-substituted allylic carbonates to α,β-unsaturated imines, allowing facile access to versatile oxazocines in good yields with excellent b/l and Z/E selectivities (up to 92% yield and complete b/l and Z/E selectivities). The reaction exhibited a broad substrate scope, mild reaction conditions, and good functional group compatibility. In addition, an asymmetric version has also been tested, affording the desired oxazocines in moderate to good enantioselectivity.
Key words
palladium catalysis - Mengphos - [4+4] cycloaddition - α,β-unsaturated imines - allyl carbonates - oxazocinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2435-5589.
- Supporting Information
Publication History
Received: 02 August 2024
Accepted after revision: 07 October 2024
Accepted Manuscript online:
07 October 2024
Article published online:
04 November 2024
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